Dichloromethane → Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]amino}-1h-benzimidazol-1-yl)methyl]benzoate

HRID 1594520Notes

Reaction equation

HRID 1594520 reaction equation
[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:23][O:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=1.C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O>[Cl:20][C:19]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:32][C:29]3[CH:30]=[CH:31][C:26]([C:25]([O:24][CH3:23])=[O:34])=[CH:27][CH:28]=3)[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)=[N:6][C:5]=2[CH:18]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 694181195,6-Dichloro-N-[4-(methoxy)phenyl]-1H-benzimidazol-2-amine

Product 1

HCID 69417835Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]amino}-1h-benzimidazol-1-yl)methyl]benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To the title compound of Example 19, Step A (1.3 mmol, 407 mg) in DMF (5 mL) was added NaH (1.6 mmol, 62 mg of 60% suspension in mineral oil). After 10 min methyl-4-(bromomethyl)benzoate (1.3 mmol, 304 mg) was added and the reaction mixture was allowed to stand at ambient temperature for 2 h. Aqueous workup with CH2Cl2/saturated NaHCO3 and brine, followed by flash chromatography on silica eluting with 40%, 50% and 60% EtOAc in hexanes afforded the product as a tan solid. LC-MS (ESI, Method B): 1.93 min, m/z 456.1 (M+1).

Sources & evidence

ORD record
ord-56ddd106182446ac83db84a1af51889d
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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